The present invention relates to a composition comprising
(a) from 1 to 20, preferably from 1 to 10% by weight of a sorbitan ester of the formula I 
wherein R1 and R2, independently from each other, stand for C1-C20alkyl or C2-C20alkenyl, and
(b) from 99 to 80, preferably from 99 to 90% by weight of a metal or ammonium laked monoazo pigment of formula 11 
xe2x80x83wherein
R3, R4, R5, R6, R7 and R8 independently from each other stand for hydrogen, C1-C20alkyl C1-C20alkoxy, C2-C20alkenyl, C1-C20alkylthiol, C1-C20alkoxycarbonyl, hydroxyC1-C4alkoxy, phenyl, benzyl, phenylthio, fluoro, chloro, bromo, iodo, xe2x80x94CN, xe2x80x94NO2, xe2x80x94CF3, xe2x80x94COR9, xe2x80x94COOR9, xe2x80x94CONR9R10, xe2x80x94SO2R9, xe2x80x94SO2NR9R10, xe2x80x94NR9NR10 in which each R9 and R10 are each independently from each other hydrogen, xe2x80x94OH, C1-4-alkyl or phenyl, where at least one of R3, R4, R5, R6, R7 and R8 is either xe2x80x94COOH or xe2x80x94SO3H, and M may be NH4+, or a cation of an alkali metal, an alkaline earth metal, such as Na, K, Mg, Ca, Sr, Ba, or a cation of a transition metal such as Mn, Co, Ni, Cu, Fe or Al,
as well as a process for its preparation and its use as well as the use of the sorbitan ester I as an additive to improve color strength and dispersion properties.
WO 9851160 describes a pigment or dyestuff composition comprising 2 to 10% by weight of a pigment or dyestuff, 3 to 30% by weight of a polyoxyethylene sorbitan fatty acid ester, 1 to 10% by weight of another sorbitan fatty acid ester and dispersing agents.
JP-A2 10204243 describes vinylidene chloride-based polymer compositions with improved dispersibility for coloration of polymers comprising the polymer, 30% by weight Pigment Red 208, 2% by weight sorbitan trioleate and other additives.
U.S. Pat. No. 4,177,082 describes nondusting, easily dispersible pigment or dye granules, wherein a pigment is treated with a mixture of hydroxyethylcellulose, an amine, sorbitan tristearate and dicyclohexyl phthalate under elevated temperature, then pH adjusting and finally mixing with a polymer such as polyvinylchloride (xe2x80x9cPVCxe2x80x9d) or polyethylene (xe2x80x9cPExe2x80x9d).
JP-A2 50101427 describes compositions comprising a pigment, PVC, diphenol derivatives and polyethylene glycol sorbitan monolaurate. According to this document the addition of bisphenol A is essential for a good dispersibility.
However, the dispersibility and color strength of the abovementioned compositions is not good enough for todays demands. Further, in all cases the pigments and the additives, inter alia sorbitan fatty acid esters, are mixed together at the same time. In addition, compositions consisting of just a pigment and sorbitan fatty acid esters are not known, rather, always additional additives have to be used, too.
Hence, the object of this invention was to provide compositions consisting of a metal or ammonium laked monoazo pigments with improved color strength and dispersion properties. Especially, an object was to improve the color strength and dispersion properties of Pigment Yellow 191:1 by the addition of an appropriate additive. In addition, the inventive composition should be used in food contact applications.
Accordingly, the above defined composition was found.
Metal or ammonium laked monoazo pigments such as Pigment Yellow 61, Pigment Yellow 62:1, Pigment Yellow 100, Pigment Yellow 133, Pigment Yellow 168, Pigment Yellow 169, Pigment Yellow 183 (e.g. Paliotol(copyright)Yellow K-2270 from BASF), Pigment Yellow 190 (e.g. PV Fast yellow HGR from Hoechst), and Pigment Yellow 191:1 are well known to the person skilled in the art, e.g. from Herbst/Hunger, xe2x80x9cIndustrielle Organische Pigmentexe2x80x9d, 2nd edition, VCH 1995, p. 240-243.
A preferred embodiment of the present invention relates to a composition consisting essentially of
(a) from 1 to 10% by weight of sorbitan ester I, preferably wherein R1=R2=C8-C20alkyl or C8-C20alkenyl, and
(b) from 99 to 90% by weight of compound II or compound III, preferably wherein R3, R4, R5, R6, R7 and R8 independently from each other stand for hydrogen, methyl, methoxy, fluoro, chloro, bromo, iodo, xe2x80x94NO2, xe2x80x94CF3, xe2x80x94COOR9, xe2x80x94SO2R9, in which R9 preferably stands for hydrogen or xe2x80x94OH, and more preferred, wherein at least one of R3, R4, R5, R6, R7 and R8 independently from each other, stand for xe2x80x94COOH or xe2x80x94SO3H, and wherein M stands for ammonium, or a cation of Ca, Sr or Al.
Another preferred embodiment of the instant invention relates to a composition consisting essentially of
(a) from 1 to 10% by weight of a sorbitan ester I, wherein R1 stands for n-undecyl, and
(b) from 90 to 99% by weight of a laked monoazo derivative of formula IIIa 
A particularly preferred embodiment relates to a composition consisting of
(a) 95% by weight of monoazo derivative IIIa and
(b) 5% by weight of sorbitan monolaurate.
A further particularly preferred embodiment relates to a composition consisting of
(a) 95% by weight of 
(b) 5% by weight of sorbitan monostearate.
C1-C20alkyl stands for methyl, ethyl, n-, i-propyl, n-, i-, sec.-, tert.-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, preferably C8-C20alkyl such as n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl;
C1-C4alkyl stands for methyl, ethyl, n-, i-propyl, n-, i-, sec.-, tert.-butyl;
C1-C20alkoxy stands for methoxy, ethoxy, n-, i-propoxy, n-, i-, sec.-, tert.-butoxy, n-pentoxy, n-hexoxy, n-heptoxy, n-octoxy, n-nonoxy, n-decoxy, n-undecoxy, n-dodecoxy, n-tridecoxy, n-tetradecoxy, n-pentadecoxy, n-hexadecoxy, n-heptadecoxy, n-octadecoxy, n-nonadecoxy, n-eicosoxy;
C2-C20alkenyl stands for ethenyl, n-, i-propenyl, n-, i-, sec.-, tert.-butenyl, n-pentenyl, n-hexenyl, n-heptenyl, n-octenyl, n-nonenyl, n-decenyl, n-undecenyl, n-dodecenyl, n-tridecenyl, n-tetradecenyl, n-pentadecenyl, n-hexadecenyl, n-heptadecenyl, n-octadecenyl, n-nonadecenyl, n-eicosenyl;
C1-C20alkylthiol stands for methylthio, ethylthio, n-, i-propylthio, n-, i-, sec.-, tert.-butylthio, n-pentylthio, n-hexylthio, n-heptylthio, n-octylthio, n-nonylthio, n-decylthio, n-undecylthio, n-dodecylthio, n-tridecylthio, n-tetradecylthio, n-pentadecylthio, n-hexadecylthio, n-heptadecylthio, n-octadecylthio, n-nonadecylthio, n-eicosylthio;
C1-C20alkoxycarbonyl stands for methoxycarbonyl, ethoxycarbonyl, n-, i-propoxycarbonyl, n-, i-, sec.-, tert.-butoxycarbonyl, n-pentoxycarbonyl, n-hexoxycarbonyl, n-heptoxycarbonyl, n-octoxycarbonyl, n-nonoxycarbonyl, n-decoxycarbonyl, n-undecoxycarbonyl, n-dodecoxycarbonyl, n-tridecoxycarbonyl, n-tetradecoxycarbonyl, n-pentadecoxycarbonyl, n-hexadecoxycarbonyl, n-heptadecoxycarbonyl, n-octadecoxycarbonyl, n-nonadecoxycarbonyl, n-eicosoxycarbonyl;
hydroxyC1-C4alkoxy hydroxymethoxy, hydroxyethoxy, hydroxy-n-, -i-propoxy, hydroxy-n-, -i-, -sec.-, -tert.-butoxy;
M may be NH4+, or a cation of an alkali metal, an alkaline earth metal, such as Na, K, Mg, Ca, Sr, Ba, or a cation of a transition metal such as Mn, Co, Ni, Cu, Fe or from Al.
Another embodiment of the present invention is directed to a process for the preparation of the inventive compositions, wherein
(a) a mixture of a pigment of formula II or III, sorbitan ester I and water is heated to a temperature in the range of 70 to 100xc2x0 C., preferably to reflux, for 1 to 60 minutes, then
(b) cooling the obtained mixture to a temperature in the range of from 30 to 70xc2x0 C., then
(c) separation of the solid parts from the liquid parts,
(d) drying the obtained solid parts at a temperature in the range of from 50 to 90xc2x0 C., and
(e) optionally sieving the thus dried pigment composition to the desired particle size.
Another preferred embodiment relates to a process for the preparation of the inventive composition characterized in
(a) reacting an amino compound of formula IV 
xe2x80x83with sodium nitrite,
(b) reacting the thus obtained diazo component with either 
(c) adding an effective amount of a metal salt or ammonium salt, MX, wherein X stands for an anion, to the reaction mixture obtained in (b) or during one of the reaction steps (a) and/or (b),
(d) adding a sorbitan ester I to the reaction mixture obtained in (b) or during one of the reaction steps (a) and/or (b).
The general synthesis is known to the skilled artisan, e.g. from U.S. Pat. No. 5,151,505.
Another embodiment of the present invention is related to a method of coloring high molecular weight organic materials (having a molecular weight usually in the range of from 103 to 107 g/mol) by incorporating the inventive compositions I by known methods in the art. As high molecular weight organic materials the following can be used such as biopolymers, and plastic materials, including fibres.
Illustrative examples of suitable organic materials of high molecular weight which can be colored with the inventive compositions of this invention are vinyl polymers, for example poly-styrene, poly-xcex1-methylstyrene, poly-p-methylstyrene, poly-p-hydroxystyrene, poly-p-hydroxy-phenylstyrene, polymethyl methacrylate and polyacrylamide as well as the corresponding methacrylic compounds, polymethylmaleate, polyacrylonitrile, polymethacrylonitrile, polyvinyl chloride, polyvinyl fluoride, polyvinylidene chloride, polyvinylidene fluoride, polyvinyl acetate, polymethyl vinyl ether and polybutyl vinyl ether; polymers which are derived from maleinimide and/or maleic anhydride, such as copolymers of maleic anhydride with styrene; polyvinyl pyrrolidone; ABS; ASA; polyamides; polyimides; polyamidimides; polysulfones; polyether sulfones; polyphenylene oxides; polyurethanes; polyureas; polycarbonates; polyarylenes; polyarylene sulfides; polyepoxides; polyolefins such as polyethylene and polypropylene; polyalkadienes; biopolymers and the derivatives thereof e.g. cellulose, cellulose ethers and esters such as ethylcellulose, nitrocellulose, cellulose acetate and cellulose butyrate, starch, chitin, chitosan, gelatin, zein; natural resins; synthetic resins such as alkyd resins, acrylic resins, phenolic resins, epoxide resins, aminoformaldehyde resins such as urea/formaldehyde resins and melamine/formaldehyde resin; vulcanized rubber; casein; silicone and silicone resins; rubber, chlorinated rubber; and also polymers which are used, for example, as binders in paint systems, such as novolaks which are derived from C1-C6-aldehydes such as formaldehyde and acetaldehyde and a binuclear or mononuclear, preferably mononuclear, phenol which, if desired, is substituted by one or two C1-C9alkyl groups, one or two halogen atoms or one phenyl ring, such as o-, m- or p-cresol, xylene, p-tert.-butylphenol, o-, m- or p-nonylphenol, p-chlorophenol or p-phenylphenol, or a compound having more than one phenolic group such as resorcinol, bis(4-hydroxyphenyl)methane or 2,2-bis(4-hydroxyphenyl)propane; as well as suitable mixtures of said materials.
Particularly preferred high molecular weight organic materials, in particular for the preparation of a paint system, a printing ink or ink, are, for example, cellulose ethers and esters, e.g. ethylcellulose, nitrocellulose, cellulose acetate and cellulose butyrate, natural resins or synthetic resins (polymerization or condensation resins) such as aminoplasts, in particular urea/formaldehyde and melamine/formaldehyde resins, alkyd resins, phenolic plastics, poly-carbonates, polyolefins, polystyrene, polyvinyl chloride, polyamides, polyurethanes, poly-ester, ABS, ASA, polyphenylene oxides, vulcanized rubber, casein, silicone and silicone resins as well as their possible mixtures with one another.
In a particularly preferred embodiment of this invention, the inventive compositions are used for the mass coloration of polyvinyl chloride, polyamides and, especially, polyolefins such as polyethylene and polypropylene.
According to observations made to date, the inventive compositions can be added in any desired amount to the material to be colored, depending on the end use requirements. In the case of high molecular weight organic materials, for example, the compositions prepared according to this invention can be used in an amount in the range from 0.01 to 40, preferably from 0.01 to 5% by weight, based on the total weight of the colored high molecular weight organic material.
Hence, another embodiment of the present invention relates to a composition comprising
(a) 0.01 to 50, preferably 0.01 to 5, particularly preferred 0.01 to 2% by weight, based on the total weight of the colored high molecular organic material, of a composition according to the present invention, and
(b) 99.99 to 50, preferably 99.99 to 95, particularly preferred 99.99 to 98% by weight, based on the total weight of the colored high molecular organic material, of a high molecular organic material, and
(c) if desired, customary additives such as rheology improvers, dispersants, fillers, paint auxiliaries, siccatives, plasticizers, UV-stabilizers, and/or additional pigments or corresponding precursors in effective amounts, such as e.g. from 0 to 50% by weight, based on the total weight of (a) and (b).
To produce non-brittle mouldings or to diminish their brittleness, so-called plasticizers can be added to the high molecular weight organic materials prior to moulding. Plasticizers may be, for example, esters of phosphoric acid, phthalic acid and sebacic acid. Said plasticizers may be added before, during or after pigmenting the high molecular weight organic materials with the inventive compositions.
To obtain different shades, the inventive compositions may advantageously be used in admixture with fillers, transparent and opaque white, colored and/or black pigments as well as customary luster pigments in the desired amount.
A further embodiment of the present invention relates to a method of using the inventive compositions for the preparation of dispersions and the corresponding dispersions comprising the inventive compositions.
In addition to, or in place of the preferred polymeric dispersants, surfactants may be used as dispersants. These may be anionic, nonionic, or amphoteric surfactants. A detailed list of non-polymeric as well as some polymeric dispersants is disclosed in the section on dispersants of Manufacturing Confection Publishing Co., (1990) p. 110-129, McCutcheon""s Functional Materials, North America Edition.
For the pigmentation of high molecular weight organic material, the inventive compositions, optionally in the form of masterbatches, usually are mixed with the high molecular weight organic materials using roll mills, mixing apparatus or grinding apparatus. Generally, the pigmented material is subsequently brought into the desired final form by conventional processes, such as calandering, compression molding, extrusion, spreading, casting or injection molding. In order to prepare non-rigid moldings or to reduce their brittleness it is often desired to incorporate so-called plasticizers into the high molecular weight organic materials prior to forming. Examples of compounds which can be used as such plasticizers are esters of phosphoric acid, phthalic acid or sebacic acid. The plasticizers can be added before or after the incorporation of the inventive compositions into the polymers. It is also possible, in order to achieve different hues, to add fillers or other coloring constituents such as white, color or black pigments in desired amounts to the high molecular weight organic materials in addition to the inventive compositions.
A further embodiment of the present invention relates to the use of the sorbitan ester I as an additive to improve color strength and dispersibility of metal or ammonium laked monoazo pigments, preferably of the pigments II or III.
Plastics and fibres pigmented with the inventive compositions exhibit superior color strength and the pigments dispersed therein exhibit superior dispersibility.